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Progress in Medicinal Chemistry, Volume 26
BOOK REVIEWS Chronopharmacology. Edited by Bjorn Lemmer. Marcel Dekker: New York, 1989. 744 pp. 26 x 8.5 cm. ISBN 08247-8103-1. $150.00. The Gershwin brothers’ song “I Got Rhythm” is the leitmotif for this 3lchapter, 49-author book. The editor notes that “Chronopharmacology has developed into a science that is gaining more and more importancefor drug treatment. Thus the time has come to bring together an inclusive presentation of recent developments in chronopharmacology.”There is a s u b theme: there are two kinds of phmacologistschronopharmacologists and others, variously called “classical” or “homeostatic” pharmacologists.Sociologistsof science will find a group of under-appreciated chronos trying to convert a homeostatic majority who can’t, or won’t, grasp the Gershwins’message. On their part, homeostats have the daunting task of formally proving drug efficacy a t any time, and are skeptical about having to redo it around the clock. Chronosoffer hope of widened therapeutic indices at special times. The editor was passive: style, content, and both graphical and bibliographical formats oscillate, though the index appears to be good. Graphical formats are noteworthy, because many will scan the book to see the bigger rhythms. Scanners beware: the expanded ordinate, with the origin off the bottom ofthe page, is a chronotrademark. Editorial palsy shows, with adjacent chapters on asthma reproducing the same figure, only one having an adequate legend. Nonetheless, asthma, with its tendency to predawn worsening, is one of the better chronostories, with good supporting data. Probably the most informative chapter for readers of this journal is by John Moore. Earlier chapters are deserts of chronophenomenology compared to Moore’s oasis of physiological insight. It lucidly describes the several chronocurved balls that the gut throws at drug researchers. Moore also gives interesting clues on how to design NSAID regimens most likely to confer competitive advantage. A stunning omission is the story of pulsatile gonadotropinreleasing hormone (GnRH) therapy for infertility. Two decades ago Knobil’s group discovered the pulsatile secretion of GnRH in monkeys, showing that a GnRH pulse every 60-90 minutes maintains cyclic pituitary gonadotropin secretion and ovulation, and can restore both when endogenous GnRH is lacking. Yet GnRH by infusion or by pulses outside a rather narrow frequency range turn this pituitary activator into an inhibitor. Today, these precepts are the foundation for restoring fertility in women with hypothalamic amenorrhea. Pulsatile GnRH treatment is by far the most dramatic and complete chronostory; with only a fleeting reference to it in a chapter on another topic, this book, which purports to be inclusive, is mislabeled.
forms. An appreciation of preformulation studies significantly increases the ease with which formulation development takes place, leading to products which are stable. Dr. James Wells approaches preformulation testing assuming that only a limited quantity of bulk drug is available, which is often the case, and develops a work program to generate important fundamental physical and chemical properties of the drug molecules and the drug powder. Needless to say, this information dictates the subsequent events and approaches in formulation development. The author has outlined a pragmatic approach often supplemented with practical examples from his industrial experience as well as published literature illustrating the underlying theory. The book is organized into eight chapters. The first chapter introduces the structured program for drug characterization and, thus, the format of the book. The preformulation tests discussed are divided according to the fundamental (e.g., solubility, pK,, melting point) and the derived properties (e.g., powder flow and compression properties) of the drug. Chapter 2 deals extensively with solubility and has in-depth discussion of intrinsic solubility, pK,, partition coefficients, dissolution, and salt-form selection. The third chapter covers polymorphism, purity determination, and the relationship between melting point and solubility. Analytical method development using LW spectroscopy, TLC, and HPLC for drug stability assessment is the focus of another chapter. The influence of various factors such as pH, hydrolysis, photolysis, solvolysis, hygroscopicity, and temperature on drug stability is explained in the next chapter along with a good discussion on oxidation and antioxidants. The applications of microscopy for basic crystallography and particle size analysis, as well as assessment of powder flow properties, have also been briefly discussed. The reader of this book will probably be familiar with the topics discussed in the book. Each of the topics covered in this textbook has also been the subject of a book or has appeared as a chapter in other physical chemistry books. What is remarkable about this book is the style and approach the author has taken to present the material. The strength of the book is that it offers a single compilation of the concepts and approaches in preformulation. The chapters are well written and adequately referenced; the language is easy to understand. Although there are a few typographical errors, they do not diminish the value of the book. This book can serve as a textbook for an advanced course in physical pharmacy for undergraduates and first-year graduate students in pharmaceutics. Pharmaceutical research scientists and chemists and technicians in the industry will also find this book helpful and can use it as a handy reference book. The book will be a usehl addition to industrial and institutional libraries. Praful Agrawala Formulation Development Adria Laboratories Columbus, Ohio 43216
John Urquhart Chief Scientist APREX Corporation 4777 Warm Springs Blvd. Fremont, CA 94539
Pharmaceutical Preformuiatlon: The Physlcochemical Properties of Drug Substances. By James I. Wells. Ellis Horwood: Chichester, U.K. 1988. 227 pages. 17 x 24.5 cm. ISBN 0-7458-02761. $59.95. Physicochemical profiling of a drug substance is the first step towards the development of pharmaceutical dosage o O ~ - 3 ~ 9 / ~ / 0 6 O O - 0 5 5 13.OO/O $0 0 1990, American Pharmaceutical Association
Progress in Medicinal Chemistry, Volume 26. Edited by G. P. Ellis and G. B. West. Elsevier Science Publishers: Amsterdam, 1989. v + 586 pp. 15 x 21 cm. ISBN 0-444-81038-2. $197.50.
The latest volume in the series Progress in Medicinal Chemistry, this book continues the tradition of presenting reviews of topical interest in medicinal chemistry. The book contains six reviews, of which the first three deal with various Journal of Pharmaceutical Sciences I 553 Vol. 79, No. 6, June 1990
aspects of drug treatment of cancers. Chapter 1,by A. Rosowsky, is a comprehensive, up-to-date treatment of the “Chemistry and Biological Activity of Antifolates”, taking up almost half the volume; it is an excellent treatise on the subject. Literature citations are numerous and current, and the layout of the chapter, based on the structural modifications made a t different sites of the prototype methotrexate molecule will no doubt please medicinal chemists. This reviewer, however, was struck by the similarity of this chapter to a shorter one that appeared in last year’s Volume 25 in the same series, on “Synthesis of Analogues of Folic Acid, Aminopterin and Methotrexate as Antitumor Agents”, by D. C. Palmer et al. Indeed, there is quite an overlap in subject matter between the two reviews and one cannot help but question the motive of the editors in selecting such similar reviews in two consecutive volumes. Chapter 2, by L. Banting et al., deals with aromatase inhibition as a means of treating estrogen-dependent breast cancer. The review is well structured and discusses both the non-steroidal aromatase inhibitors such as aminogluthetamide and ketonazole and the steroidal substrate analogues; the structure-activity relationships are discussed well and the literature citations are current. The third chapter, on “Endocrine Treatment of Prostate Cancer”, is a brief discussion on the subject. With the exception of a few citations from the mid- to late 1980s, most deal with older literature. A considerable portion of the chapter is devoted to a discussion of clinical trials with the LH-RH decapeptide analogue, goserelin. Chapter 4, on “Microcomputers in Biomedical Education”, is directed towards educators and provides an outline of fundamental concepts of computer methodology, teaching networks and molecular modeling. The review on “Applications of Modern High-Field NMR Spectroscopy in Medicinal Chemistry” (Chapter 5),cannot hope to do full justice to this burgeoning area of research, but serves as a useful reference to initiate researchers into the potential applications of NMR techniques in drug research, such as the study of enzymesubstrate complexes, chiral resolution, and drug metabolism. It takes the unfamiliar reader through acronyms such as COSY, NOE, WEFT, and INEPT that pervade NMR literature today, and decodes some of the mystery behind “magic angle spinning (MAS)”spectroscopy. Chapter 6, by J. R. J. Sorensen, deals with the use of copper complexes in the treatment of various chronic disorders, with an emphasis on biochemical aspects of normal and abnormal copper metabolism. It updates a 1978 review on the subject in Volume 15 of this series. This book, as part of this invaluable series, is a “must have” for biomedical libraries; the price may deter all but intrepid purchasers of individual copies. Educators will find the book useful to update course material in medicinal chemistry and pharmacology. Researchers in the specific areas covered by the reviews will obviously benefit most from this volume. Irach B. Taraporewala Department of Organic Chemistry Southwest Foundation for Biomedical Research San Antonio, TX 78284-0147
554 I Journal of Pharmaceutical Sciences Vol, 79, No. 6, June 1990
Current Books Antieplleptlc Drugs. 3rd Ed. Edited by F. E. Dreifuss, Richard H. Mattson, Brain S. Meldrum, and J. Kiffin Penry. Raven Press: New York. 1989. xxvii + 1025 pp. 26 x 19 cm. ISBN 0-881 67-539-3. Price not given. Chlral Liquid Chromatography. Edited by W. J. Lough. BlackieChapman and Hall: New York. ix + 276 pp. 24 x 16 cm. ISBN 0-412-01 741-5. $1 12.00.
Data Analysis in the Chemlcal Industry. Voi. 1: Basic Techniques. By Roland Caulcutt. Halsted Press: Chichester, U.K. 1989.228 pp. 25 x 17 cm. ISBN 0470-21492-9. Price not given. Sulfur-Containing Drugs and Related Organlc Compounds. Edited by L. A. Damani. Halsted Press: Chichester, U.K. 1989. 175 pp. 25 x 17 cm. ISBN 0470-21501-1. $74.95. Pharmaceutlcal Thermal Analysls. Techniques and Applications. By James L. Ford and Peter Timmins. Halsted Press: Chichester,U.K. 1989. 313 pp. 25 x 17 cm. ISBN 0-470-21219-5. $99.95. Computer Aided Drug Design. Methods and Applications, Edited by Thomas J. Perun and C. L. Propst. Marcel Dekker: New York. 1989. xii + 493 pp. 24 x 16 cm. ISBN 0-8247-8037-X. $99.75. Steroid Analysis In the Pharmaceutical industry. Edited by S. Gorog. Ellis Hotwood: Chichester, U.K. 1989. xi + 398 pp. 25 x 17 cm. ISBN 0-470-21 178-4. $94.95.
Drug Research and Drug Development In the 21st Century. Edited by H. P. Wolff, A. Fleckenstein, and E. Philipp. Springer-Verlag:Berlin. 1989.xii + 310pp. 24 x 17cm. ISBN 3-540-50961-5. Price notgiven. Cytoklnes In Cancer Therapy. By Frances R. Balkwill. Oxford University Press: Oxford, U.K. 1989. xvi + 297 pp. 24 x 16 cm. ISBN 0-19-261715-X. Price not given. Drug Formulation. By 1. Racz. John Wiley: New York. 1989. ix + 416 pp. 25 x 17 cm. ISBN 0471-90517-8. $133.00. Human Drug Kinetics: A Course of Simulated Experlments. By L. Saunders, D. Ingrarn, and S. H. D. Jackson. IRL Press: Oxford, UK. 1989. xxii + 261 pp. 24 x 17 cm. ISBN 0-19-963038-0. $35.00. Prlnclples of Cllnlcal Toxicology. 2nd Edition. By Thomas A. Gossel and J. Douglas Bricker. Raven Press: New York. 1989. xii + 413 pp. 26 x 18 cm. ISBN 0-88167-551-2. Price not given. Antlepileptlc Drug Interactions. Edited by William H. Pitlick. Demos Publications: New York, 1989. xiv + 338 pp. 24 x 16 cm. ISBN 0-939957-14-0. Price not given. Targeted TherapeuticSystems. Edited by Praveen Tyle and Bhanu P. Ram. Marcel Dekker: New York. 1990. xv + 388 pp. 24 x 16 cm. ISBN 0-8247-8181-3. $125.00.
Blosynthetlc Products for Cancer Chemotherapy. By George R. Pettit, Cherry L. Herald, Cecil R. Smith. Elsevier Science:Amsterdam. 1989. xiv + 400 pp. 27 x 20 cm. ISBN 0-444-88049-6. $141.50. Modern Pharmaceutlcs. Second Edition. Edited by Gilbert S. Banker and Christopher T. Rhodes. Marcel Dekker: NY. 1990. xiv + 888 pp. 26 x 18 cm. ISBN 0-8247-7499-X.$125.00. Chromatography/Fourler Transform. Infrared Spectroscopy and Its Applications. By Robert White. Marcel Dekker: New York. 1990. vi + 328 pp. 24 x 16 cm. ISBN 0-8247-8191-0. $99.75. Statistical Issues In Drug Research and Development. Edited by Karl E. Peace. Marcel Dekker: New York. 1990. xi + 366 pp. 24 x 16 cm. ISBN 0-8247-8290-9. $99.75.
Chromatographic Analysis of Pharmaceuticals. Edited by John A. Adamovics.Marcel Dekker: New York. 1990. ix + 661 pp. 24 x 16 cm. ISBN 0-8247-7953-3.$125.00.
Multldlmenslonal Chromatography. Techniques and Applications. Edited by Hernan J. Cortes. Marcel Dekker: New York. 1990. viii + 378 p. 24 x 16 cm. ISBN 0-8247-8136-8. $99.75. Readers: If you wish to review one of the books ilsted above, contact Margaret H. Sickels, Assistant Editor, (202) 429-7518.
forms. An appreciation of preformulation studies significantly increases the ease with which formulation development takes place, leading to products which are stable. Dr. James Wells approaches preformulation testing assuming that only a limited quantity of bulk drug is available, which is often the case, and develops a work program to generate important fundamental physical and chemical properties of the drug molecules and the drug powder. Needless to say, this information dictates the subsequent events and approaches in formulation development. The author has outlined a pragmatic approach often supplemented with practical examples from his industrial experience as well as published literature illustrating the underlying theory. The book is organized into eight chapters. The first chapter introduces the structured program for drug characterization and, thus, the format of the book. The preformulation tests discussed are divided according to the fundamental (e.g., solubility, pK,, melting point) and the derived properties (e.g., powder flow and compression properties) of the drug. Chapter 2 deals extensively with solubility and has in-depth discussion of intrinsic solubility, pK,, partition coefficients, dissolution, and salt-form selection. The third chapter covers polymorphism, purity determination, and the relationship between melting point and solubility. Analytical method development using LW spectroscopy, TLC, and HPLC for drug stability assessment is the focus of another chapter. The influence of various factors such as pH, hydrolysis, photolysis, solvolysis, hygroscopicity, and temperature on drug stability is explained in the next chapter along with a good discussion on oxidation and antioxidants. The applications of microscopy for basic crystallography and particle size analysis, as well as assessment of powder flow properties, have also been briefly discussed. The reader of this book will probably be familiar with the topics discussed in the book. Each of the topics covered in this textbook has also been the subject of a book or has appeared as a chapter in other physical chemistry books. What is remarkable about this book is the style and approach the author has taken to present the material. The strength of the book is that it offers a single compilation of the concepts and approaches in preformulation. The chapters are well written and adequately referenced; the language is easy to understand. Although there are a few typographical errors, they do not diminish the value of the book. This book can serve as a textbook for an advanced course in physical pharmacy for undergraduates and first-year graduate students in pharmaceutics. Pharmaceutical research scientists and chemists and technicians in the industry will also find this book helpful and can use it as a handy reference book. The book will be a usehl addition to industrial and institutional libraries. Praful Agrawala Formulation Development Adria Laboratories Columbus, Ohio 43216
John Urquhart Chief Scientist APREX Corporation 4777 Warm Springs Blvd. Fremont, CA 94539
Pharmaceutical Preformuiatlon: The Physlcochemical Properties of Drug Substances. By James I. Wells. Ellis Horwood: Chichester, U.K. 1988. 227 pages. 17 x 24.5 cm. ISBN 0-7458-02761. $59.95. Physicochemical profiling of a drug substance is the first step towards the development of pharmaceutical dosage o O ~ - 3 ~ 9 / ~ / 0 6 O O - 0 5 5 13.OO/O $0 0 1990, American Pharmaceutical Association
Progress in Medicinal Chemistry, Volume 26. Edited by G. P. Ellis and G. B. West. Elsevier Science Publishers: Amsterdam, 1989. v + 586 pp. 15 x 21 cm. ISBN 0-444-81038-2. $197.50.
The latest volume in the series Progress in Medicinal Chemistry, this book continues the tradition of presenting reviews of topical interest in medicinal chemistry. The book contains six reviews, of which the first three deal with various Journal of Pharmaceutical Sciences I 553 Vol. 79, No. 6, June 1990
aspects of drug treatment of cancers. Chapter 1,by A. Rosowsky, is a comprehensive, up-to-date treatment of the “Chemistry and Biological Activity of Antifolates”, taking up almost half the volume; it is an excellent treatise on the subject. Literature citations are numerous and current, and the layout of the chapter, based on the structural modifications made a t different sites of the prototype methotrexate molecule will no doubt please medicinal chemists. This reviewer, however, was struck by the similarity of this chapter to a shorter one that appeared in last year’s Volume 25 in the same series, on “Synthesis of Analogues of Folic Acid, Aminopterin and Methotrexate as Antitumor Agents”, by D. C. Palmer et al. Indeed, there is quite an overlap in subject matter between the two reviews and one cannot help but question the motive of the editors in selecting such similar reviews in two consecutive volumes. Chapter 2, by L. Banting et al., deals with aromatase inhibition as a means of treating estrogen-dependent breast cancer. The review is well structured and discusses both the non-steroidal aromatase inhibitors such as aminogluthetamide and ketonazole and the steroidal substrate analogues; the structure-activity relationships are discussed well and the literature citations are current. The third chapter, on “Endocrine Treatment of Prostate Cancer”, is a brief discussion on the subject. With the exception of a few citations from the mid- to late 1980s, most deal with older literature. A considerable portion of the chapter is devoted to a discussion of clinical trials with the LH-RH decapeptide analogue, goserelin. Chapter 4, on “Microcomputers in Biomedical Education”, is directed towards educators and provides an outline of fundamental concepts of computer methodology, teaching networks and molecular modeling. The review on “Applications of Modern High-Field NMR Spectroscopy in Medicinal Chemistry” (Chapter 5),cannot hope to do full justice to this burgeoning area of research, but serves as a useful reference to initiate researchers into the potential applications of NMR techniques in drug research, such as the study of enzymesubstrate complexes, chiral resolution, and drug metabolism. It takes the unfamiliar reader through acronyms such as COSY, NOE, WEFT, and INEPT that pervade NMR literature today, and decodes some of the mystery behind “magic angle spinning (MAS)”spectroscopy. Chapter 6, by J. R. J. Sorensen, deals with the use of copper complexes in the treatment of various chronic disorders, with an emphasis on biochemical aspects of normal and abnormal copper metabolism. It updates a 1978 review on the subject in Volume 15 of this series. This book, as part of this invaluable series, is a “must have” for biomedical libraries; the price may deter all but intrepid purchasers of individual copies. Educators will find the book useful to update course material in medicinal chemistry and pharmacology. Researchers in the specific areas covered by the reviews will obviously benefit most from this volume. Irach B. Taraporewala Department of Organic Chemistry Southwest Foundation for Biomedical Research San Antonio, TX 78284-0147
554 I Journal of Pharmaceutical Sciences Vol, 79, No. 6, June 1990
Current Books Antieplleptlc Drugs. 3rd Ed. Edited by F. E. Dreifuss, Richard H. Mattson, Brain S. Meldrum, and J. Kiffin Penry. Raven Press: New York. 1989. xxvii + 1025 pp. 26 x 19 cm. ISBN 0-881 67-539-3. Price not given. Chlral Liquid Chromatography. Edited by W. J. Lough. BlackieChapman and Hall: New York. ix + 276 pp. 24 x 16 cm. ISBN 0-412-01 741-5. $1 12.00.
Data Analysis in the Chemlcal Industry. Voi. 1: Basic Techniques. By Roland Caulcutt. Halsted Press: Chichester, U.K. 1989.228 pp. 25 x 17 cm. ISBN 0470-21492-9. Price not given. Sulfur-Containing Drugs and Related Organlc Compounds. Edited by L. A. Damani. Halsted Press: Chichester, U.K. 1989. 175 pp. 25 x 17 cm. ISBN 0470-21501-1. $74.95. Pharmaceutlcal Thermal Analysls. Techniques and Applications. By James L. Ford and Peter Timmins. Halsted Press: Chichester,U.K. 1989. 313 pp. 25 x 17 cm. ISBN 0-470-21219-5. $99.95. Computer Aided Drug Design. Methods and Applications, Edited by Thomas J. Perun and C. L. Propst. Marcel Dekker: New York. 1989. xii + 493 pp. 24 x 16 cm. ISBN 0-8247-8037-X. $99.75. Steroid Analysis In the Pharmaceutical industry. Edited by S. Gorog. Ellis Hotwood: Chichester, U.K. 1989. xi + 398 pp. 25 x 17 cm. ISBN 0-470-21 178-4. $94.95.
Drug Research and Drug Development In the 21st Century. Edited by H. P. Wolff, A. Fleckenstein, and E. Philipp. Springer-Verlag:Berlin. 1989.xii + 310pp. 24 x 17cm. ISBN 3-540-50961-5. Price notgiven. Cytoklnes In Cancer Therapy. By Frances R. Balkwill. Oxford University Press: Oxford, U.K. 1989. xvi + 297 pp. 24 x 16 cm. ISBN 0-19-261715-X. Price not given. Drug Formulation. By 1. Racz. John Wiley: New York. 1989. ix + 416 pp. 25 x 17 cm. ISBN 0471-90517-8. $133.00. Human Drug Kinetics: A Course of Simulated Experlments. By L. Saunders, D. Ingrarn, and S. H. D. Jackson. IRL Press: Oxford, UK. 1989. xxii + 261 pp. 24 x 17 cm. ISBN 0-19-963038-0. $35.00. Prlnclples of Cllnlcal Toxicology. 2nd Edition. By Thomas A. Gossel and J. Douglas Bricker. Raven Press: New York. 1989. xii + 413 pp. 26 x 18 cm. ISBN 0-88167-551-2. Price not given. Antlepileptlc Drug Interactions. Edited by William H. Pitlick. Demos Publications: New York, 1989. xiv + 338 pp. 24 x 16 cm. ISBN 0-939957-14-0. Price not given. Targeted TherapeuticSystems. Edited by Praveen Tyle and Bhanu P. Ram. Marcel Dekker: New York. 1990. xv + 388 pp. 24 x 16 cm. ISBN 0-8247-8181-3. $125.00.
Blosynthetlc Products for Cancer Chemotherapy. By George R. Pettit, Cherry L. Herald, Cecil R. Smith. Elsevier Science:Amsterdam. 1989. xiv + 400 pp. 27 x 20 cm. ISBN 0-444-88049-6. $141.50. Modern Pharmaceutlcs. Second Edition. Edited by Gilbert S. Banker and Christopher T. Rhodes. Marcel Dekker: NY. 1990. xiv + 888 pp. 26 x 18 cm. ISBN 0-8247-7499-X.$125.00. Chromatography/Fourler Transform. Infrared Spectroscopy and Its Applications. By Robert White. Marcel Dekker: New York. 1990. vi + 328 pp. 24 x 16 cm. ISBN 0-8247-8191-0. $99.75. Statistical Issues In Drug Research and Development. Edited by Karl E. Peace. Marcel Dekker: New York. 1990. xi + 366 pp. 24 x 16 cm. ISBN 0-8247-8290-9. $99.75.
Chromatographic Analysis of Pharmaceuticals. Edited by John A. Adamovics.Marcel Dekker: New York. 1990. ix + 661 pp. 24 x 16 cm. ISBN 0-8247-7953-3.$125.00.
Multldlmenslonal Chromatography. Techniques and Applications. Edited by Hernan J. Cortes. Marcel Dekker: New York. 1990. viii + 378 p. 24 x 16 cm. ISBN 0-8247-8136-8. $99.75. Readers: If you wish to review one of the books ilsted above, contact Margaret H. Sickels, Assistant Editor, (202) 429-7518.